Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H19N2O5S.Na |
Molecular Weight | 386.398 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCCCNC1=C(OC2=CC=CC=C2)C(=CC(=C1)C([O-])=O)S(N)(=O)=O
InChI
InChIKey=QDFGOJHAQZEYQL-UHFFFAOYSA-M
InChI=1S/C17H20N2O5S.Na/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13;/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23);/q;+1/p-1
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C17H19N2O5S |
Molecular Weight | 363.408 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.rxlist.com/bumex-drug/side-effects-interactions.htm
https://www.drugs.com/cdi/bumetanide.html
http://www.wikidoc.org/index.php/Bumetanide_(oral)
Curator's Comment: description was created based on several sources, including:
http://www.rxlist.com/bumex-drug/side-effects-interactions.htm
https://www.drugs.com/cdi/bumetanide.html
http://www.wikidoc.org/index.php/Bumetanide_(oral)
Bumetanide is indicated for the treatment of edema associated with congestive heart failure, hepatic and renal disease, including the nephrotic syndrome. It blocks the reabsorption of sodium and fluid from the kidney's tubules. The most frequent clinical adverse reactions considered probably or possibly related to bumetanide are muscle cramps (seen in 1.1% of treated patients), dizziness (1.1%), hypotension (0.8%), headache (0.6%), nausea (0.6%) and encephalopathy (in patients with preexisting liver disease) (0.6%). One or more of these adverse reactions have been reported in approximately 4.1% of patients treated with Bumex (bumetanide). Lithium should generally not be given with diuretics (such as Bumex (bumetanide)) because they reduce its renal clearance and add a high risk of lithium toxicity. Bumex (bumetanide) may potentiate the effect of various antihypertensive drugs, necessitating a reduction in the dosage of these drugs.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P55011 Gene ID: 6558.0 Gene Symbol: SLC12A2 Target Organism: Homo sapiens (Human) |
3.0 µM [IC50] | ||
Target ID: Q9UP95|||O60632 Gene ID: 6560.0 Gene Symbol: SLC12A4 Target Organism: Homo sapiens (Human) |
60.0 µM [IC50] | ||
Target ID: Q9H2X9 Gene ID: 57468.0 Gene Symbol: SLC12A5 Target Organism: Homo sapiens (Human) |
55.0 µM [IC50] | ||
Target ID: Q13621 Gene ID: 6557.0 Gene Symbol: SLC12A1 Target Organism: Homo sapiens (Human) |
4.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | BUMEX Approved UseBumetanide Injection is indicated for the treatment of edema associated with congestive heart failure, hepatic and renal disease, including the nephrotic syndrome. Almost equal diuretic response occurs after oral and parenteral administration of bumetanide. Therefore, if impaired gastrointestinal absorption is suspected or oral administration is not practical, bumetanide should be given by the intramuscular or intravenous route. Successful treatment with bumetanide following instances of allergic reactions to furosemide suggests a lack of cross-sensitivity. Launch Date4.1523839E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8312869 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: FASTED |
|
111.38 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
167.34 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8312869 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: FASTED |
|
258 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.88 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3% |
BUMETANIDE serum | Homo sapiens population: HEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 mg 2 times / day multiple, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: multiple Dose: 2 mg, 2 times / day Sources: Page: p.4 |
unhealthy, 14–18 n = 21 Health Status: unhealthy Condition: Autism spectrum disorders Age Group: 14–18 Sex: M+F Population Size: 21 Sources: Page: p.4 |
Disc. AE: Hypokalemia, Anorexia... AEs leading to discontinuation/dose reduction: Hypokalemia (moderate, 14.3%) Sources: Page: p.4Anorexia (moderate) Fatigue (moderate) Polyuria (moderate, 4.8%) |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.597 |
unhealthy, 22-72 n = 18 Health Status: unhealthy Condition: Renal edema Age Group: 22-72 Sex: M+F Population Size: 18 Sources: Page: p.597 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypokalemia | moderate, 14.3% Disc. AE |
2 mg 2 times / day multiple, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: multiple Dose: 2 mg, 2 times / day Sources: Page: p.4 |
unhealthy, 14–18 n = 21 Health Status: unhealthy Condition: Autism spectrum disorders Age Group: 14–18 Sex: M+F Population Size: 21 Sources: Page: p.4 |
Polyuria | moderate, 4.8% Disc. AE |
2 mg 2 times / day multiple, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: multiple Dose: 2 mg, 2 times / day Sources: Page: p.4 |
unhealthy, 14–18 n = 21 Health Status: unhealthy Condition: Autism spectrum disorders Age Group: 14–18 Sex: M+F Population Size: 21 Sources: Page: p.4 |
Anorexia | moderate Disc. AE |
2 mg 2 times / day multiple, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: multiple Dose: 2 mg, 2 times / day Sources: Page: p.4 |
unhealthy, 14–18 n = 21 Health Status: unhealthy Condition: Autism spectrum disorders Age Group: 14–18 Sex: M+F Population Size: 21 Sources: Page: p.4 |
Fatigue | moderate Disc. AE |
2 mg 2 times / day multiple, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: multiple Dose: 2 mg, 2 times / day Sources: Page: p.4 |
unhealthy, 14–18 n = 21 Health Status: unhealthy Condition: Autism spectrum disorders Age Group: 14–18 Sex: M+F Population Size: 21 Sources: Page: p.4 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
modest [IC50 348 uM] | ||||
yes [IC50 0.75 uM] | ||||
yes [IC50 7.6 uM] | ||||
yes [IC50 77.5 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Functional comparison of the K+-Cl- cotransporters KCC1 and KCC4. | 2000 Sep 29 |
|
External Cl(-)-dependent formation of watery vacuoles by long-term hypotonic shock in 3T3-L1 cells. | 2001 |
|
Diuretic therapy and resistance in congestive heart failure. | 2001 |
|
Effect of chloride channel blockers on anti-IgE-stimulated histamine and IL-4/IL-13 release from human basophils. | 2001 Apr |
|
Insulin increases the turnover rate of Na+-K+-ATPase in human fibroblasts. | 2001 Apr |
|
Effects of thiazide- and loop-diuretics, alone or in combination, on calcitropic hormones and biochemical bone markers: a randomized controlled study. | 2001 Aug |
|
"Avian-type" renal medullary tubule organization causes immaturity of urine-concentrating ability in neonates. | 2001 Aug |
|
Protection of ischemic myocardium in diabetics by inhibition of electroneutral Na+-K+-2Cl- cotransporter. | 2001 Aug |
|
Insulin-independent, MAPK-dependent stimulation of NKCC activity in skeletal muscle. | 2001 Aug |
|
Cl(-)-dependent secretory mechanisms in isolated rat bile duct epithelial units. | 2001 Aug |
|
Contractile regulation of the Na(+)-K(+)-2Cl(-) cotransporter in vascular smooth muscle. | 2001 Aug |
|
Optical method for quantifying rates of mucus secretion from single submucosal glands. | 2001 Aug |
|
Regional differences in ciliary epithelial cell transport properties. | 2001 Aug 1 |
|
Contribution of the Na-K-Cl cotransporter on GABA(A) receptor-mediated presynaptic depolarization in excitatory nerve terminals. | 2001 Aug 15 |
|
Cisplatin-induced apoptosis of mesothelioma cells is affected by potassium ion flux modulator amphotericin B and bumetanide. | 2001 Aug 15 |
|
An integrative, in situ approach to examining K+ flux in resting skeletal muscle. | 2001 Dec |
|
Growth factors stimulate the Na-K-2Cl cotransporter NKCC1 through a novel Cl(-)-dependent mechanism. | 2001 Dec |
|
Adrenergic receptor activated ion transport in human fetal retinal pigment epithelium. | 2001 Jan |
|
Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins. | 2001 Jan |
|
Liquid and ion transport by fetal airway and lung epithelia of mice deficient in sodium-potassium-2-chloride transporter. | 2001 Jul |
|
Na+-K+-Cl- cotransporter in rat focal cerebral ischemia. | 2001 Jun |
|
cAMP-dependent fluid secretion in rat inner medullary collecting ducts. | 2001 Jun |
|
Na+ reabsorption in cultured rat epididymal epithelium via the Na+/nucleoside cotransporter. | 2001 Mar |
|
Inhibition of Na(+)/K(+)-atpase by endothelin-1 in human nonpigmented ciliary epithelial cells. | 2001 Mar |
|
HCO3- potentiates the cAMP-dependent secretory response of the human distal colon through a DIDS-sensitive pathway. | 2001 May |
|
Diverging effects of 5-HT3 receptor antagonists ondansetron and granisetron on estramustine-inhibited cellular potassium transport. | 2001 May |
|
Pulmonary oedema after ophthalmic regional anaesthesia in an unfasted patient undergoing elective surgery. | 2001 May |
|
Role of renocortical cyclooxygenase-2 for renal vascular resistance and macula densa control of renin secretion. | 2001 May |
|
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
|
Localization of a Na(+)-K(+)-2Cl(-) cotransporter in the rabbit lens. | 2001 Nov |
|
Role of Cl- current in endothelin-1-induced contraction in rabbit basilar artery. | 2001 Nov |
|
Vacuolation induced by VacA toxin of Helicobacter pylori requires the intracellular accumulation of membrane permeant bases, Cl(-) and water. | 2001 Nov 23 |
|
Ion transport and ligand binding by the Na-K-Cl cotransporter, structure-function studies. | 2001 Oct |
|
Mechanism(s) of chloride transport in human distal colonic apical membrane vesicles. | 2001 Oct |
|
Quantitative determination of the loop diuretic bumetanide in urine and pharmaceuticals by high-performance liquid chromatography with amperometric detection. | 2001 Oct |
|
Indirectly gated Cl(-)-dependent Cl(-) channels sense physiological changes of extracellular chloride in the leech. | 2001 Oct |
|
Contribution of the Na(+)-K(+)-2Cl(-) cotransporter (NKCC1) to transepithelial transport of H(+), NH(4)(+), K(+), and Na(+) in rat outer medullary collecting duct. | 2002 Apr |
|
Chloride transport in rabbit esophageal epithelial cells. | 2002 Apr |
|
Manipulation of chloride flux affects histamine-induced contraction in rabbit basilar artery. | 2002 Apr |
|
Activation of ion secretion via proteinase-activated receptor-2 in human colon. | 2002 Feb |
|
Intrinsic optical signals in the rat optic nerve: role for K(+) uptake via NKCC1 and swelling of astrocytes. | 2002 Feb |
|
Basolateral PAR-2 receptors mediate KCl secretion and inhibition of Na+ absorption in the mouse distal colon. | 2002 Feb 15 |
|
Effects of butyrate on active sodium and chloride transport in rat and rabbit distal colon. | 2002 Feb 15 |
|
Cyclic AMP-dependent Cl secretion is regulated by multiple phosphodiesterase subtypes in human colonic epithelial cells. | 2002 Jan 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Parenteral Administration: The usual initial dose is 0.5 to 1 mg intravenously or intramuscularly. Intravenous administration should be given over a period of 1 to 2 minutes. If the response to an initial dose is deemed insufficient, a second or third dose may be given at intervals of 2 to 3 hours, but should not exceed a daily dosage of 10 mg.
The usual total daily dosage of Bumetanide is 0.5 mg to 2 mg and in most patients is given as a single
dose.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17681355
10 uM of bumetanide reduced amplitude and frequency of ictal-like events (ILE) induced by 8.5 mM K(+), but it increased the frequency of ILE induced by 1 microM kainate.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 18:37:45 UTC 2023
by
admin
on
Thu Jul 06 18:37:45 UTC 2023
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Record UNII |
1QC8KM52D1
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Record Status |
Validated (UNII)
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Record Version |
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